Separation of the energetic and geometric contributions to aromaticity. 2. Analysis of the aromatic character of benzene rings in their various topological environments in the benzenoid hydrocarbons. Crystal and molecular structure of coronene

Journal of Chemical Information and Computer Sciences

Volumn 36, Issue 6, 1996, Pages 1135-1141

  Krygowski, Tadeusz Marek ^a   Cyrański, Michał ^a   Ciesielski, Arkadiusz ^a,b   Świrska, Bozena ^a   Leszczyński, Piotr ^a  

^a UNIVERSITY OF WARSAW   (Poland)

^b INSTITUTE OF BIOCHEMISTRY AND BIOPHYSICS   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010400041     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci960367g     Document Type: Article

References (29)

1. Aromaticity, Pseudoaromaticity and Antiaromaticity; Bergmann, E. D., Pullman, B., Eds.; Israel Academy of Science and Humanities: Jerusalem, 1971; Jerusalem Symp. Quant. Chem. and Biochem., Vol. III.
2. Cook, M. J.; Katritzky, A. R.; Linda, P. Aromaticity of heterocycles. Adv. Heterocycl. Chem. 1974, 17, 255-356.
3. Garratt, P. J. Aromaticity: Wiley: New York, 1986.
4. Dewar, M. J. S. A Molecular Orbital Theory of Organic Chemistry. VIII. Aromaticity and Electrocyclic Reactions. Tetrahedron Suppl. 1966, 8, 75-92.
5. Breslow, R. Small antiaromatic rings. Angew. Chem., Int. Ed. Engl. 1968, 7, 565-570.
6. Jackman, L. M.; Elvidge, J. A. Studies of aromaticity by NMR spectroscopy. Part I. 2-pyridones and related systems. J. Chem. Soc. 1961, 859-866.
7. Sondheimer, F. Recent advances in the chemistry of large-ring conjugated systems. Pure Appl. Chem. 1963, 7, 363-388.
8. Zhou, Zh. Measuring aromaticity. Int. Rev. Phys. Chem. 1992, 2, 243-261.
9. Überla, K. Faktorenanalyse; Springer-Verlag: Berlin, 1977.
10. Katritzky, A. R.; Barczyński, P.; Musumurra, G.; Pisano, D.; Szafran, M. Aromaticity as a Quantitative Concept. 1. A Statistical Demonstration of the Orthogonality of "Classical" and "Magnetic" Aromaticity in Five- and Six-Membered Heterocycles. J. Am. Chem. Soc. 1989, 111, 7-15.
11. Katritzky, A. R.; Feygelman, V.; Musumurra, G.; Barczyński, P.; Szafran, M. Aromaticity as a Quantitative Concept. 2. Sixteen Familiar Five- and Six-membered Monocyclic Heterocycles. J. Prakt. Chem. 1990, 332, 853-869.
12. Katritzky, A. R.; Feygelman, V.; Musumurra, G.; Barczyński, P.; Szafran, M. Aromaticity as a Quantitative Concept. 3. Boenzo-fused Five- and Six-membered Heterocycles. J. Prakt. Chem. 1990, 332, 870-884.
13. Katritzky, A. R.; Barczyński, P. Aromaticity as a Quantitative Concept. 4. Less Familiar Five- and Six-membered Monocyclic Heterocycles. J. Prakt. Chem. 1990, 332, 885-897.
14. Jug, K.; Koester, A. Aromaticity as a Multidimensional Phenomenon. J. Phys. Org. Chem. 1991, 4. 163-169.
15. Krygowski, T. M.: Ciesiefski, A.; Bird, C. W.; Kotschy, A. Aromatic Character of the Benzene Ring Present in Various Topological Environments in Benzenoid Hydrocarbons. Nonequivalence of Indices of Aromaticity. J. Chem. Inf. Comput. Sci. 1995, 35, 203-210.
16. Cyrański, M.; Krygowski, T. M. Structural Studies of Disubstituted Benzene Derivatives. Part II. Factor and Regression Analyses of Aromaticity of the Ring in Para-Disubstituted Benzene Derivatives. Pol. J. Chem. 1995, 69, 1088-1096.
17. Krygowski, T. M.; Cyranski, M. Separation of the energetic and geometric contributions to the aromaticity of π-electron carbocyclics. Tetrahedron. 1996, 52, 1713-1722.
18. Almenningen, A.; Bastiansen, O.: Dyvik, F. An Attempt to Determine the Structure Parameters of Condensed Ring Hydrocarbons Using the Electron-Diffraction Method in Gas Molecules. Acta Crystallogr. 1961, 14, 1056-1065.
19. Giacovazzo, C.; Burla, M. C.; Cascarano, G. The Joint Probability of Any Set of Phases Given in Any Set of Diffraction Magnitudes. I. Theoretical Considerations. Acta Crystallogr. Sect. A 1992. 48, 901-912.
20. Sheldrick, G. M. Program for the Refinement of Crystal Structures; University of Göttingen: Germany, 1993.
21. Kruszewski, J. and Krygowski, T. M. Definition of Aromaticity Basing on the Harmonic Oscillator Model. Tetrahedron Lett. 1972, 3839-3942.
22. Krygowski, T. M. Crystallographic Studies of Inter- and Intramolecular Interactions Reflected in Aromatic Character of π-Electron Systems J. Chem. Inf. Comput. Sci. 1993, 33, 70-78.
23. Krygowski, T. M.; Ciesielski, A.; Świrska, B.: Leszczyński, P. Variation of Molecular Geometry and Aromatic Character of Chrysene and Perylene in their EDA Complexes. Refinement of X-ray Crystal and Molecular Structure of Chrysene and Perylene. Pol. J. Chem. 1994, 68, 2097-2107.
24. Bird, C. W. A new aromaticity index and its application to the five-membered ring heterocycles. Tetrahedron 1985, 41, 1409-1414.
25. Krygowski, T. M.; Ciesielski, A.; Cyranski, M. Aromatic character and energy of the five- and seven-membered rings in derivatives of penta- and heptafulvenes substituted in exocyclic position. Chem. Papers 1995, 49, 128-132.
26. Allen, F. H.; Bellard, S.; Brice, M. D.; Carywright, B. A.: Doubleday, A.; Higgs, H.; Hummelink, T. W. A.; Hummelink-Peters, B, G. M. C.; Kennard, O.: Motherwell, W. D. S.; Rodgers, J. R.; Watson, D. G. The Cambridge Crystallographic Data Centre: Computer-Based Search, Retrieval, Analysis and Display of Information. Acta Crystallogr. Sect. B 1979, 35, 2331-2339.
27. Allen, F. H.; Davies, J. E.; Galloy, J. J.; Johnson, O.; Kennard, O.; McRae, C. F.; Mitchell, E. M.; Mitchell, G. F.; Smith, J. M.; Watson, D. G. The Development of Versions 3 and 4 of the Cambridge Structural Database System. J. Chem. Inf. Comput. Sci. 1991, 31, 187-204.
28. Clar, E. The Aromatic Sextet; J. Wiley & Sons: London, 1972.
29. Czermiński, J.; Iwasiewicz, A.; Paszek, Z.; Sikorski, A. Statistical Methods in Applied Chemistry; PWN - Polish Scientific Publishers: Warszawa, Elsevier: Amsterdam-Oxford-New York-Tokyo, 1990.